Cheap Flights from Charleston to Chicago
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Deals from
Charleston
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Prices updated today
451 airlines compared
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Fares are subject to change and may not be available for all dates. (Data last updated Aug 17, 2026.)
Today’s best flight deals from Charleston to Chicago
Explore current cheapest deals departing from Charleston to Chicago
2026-09-09 – 2026-09-29
CHS - Chicago
47% AI deal score
$210
$198
Round trip
2026-09-09 – 2026-09-22
CHS - Chicago
49% AI deal score
$219
$198
Round trip
2026-09-11 – 2026-09-15
CHS - Chicago
44% AI deal score
$149
$203
Round trip
2026-09-05 – 2026-09-12
CHS - Chicago
41% AI deal score
$142
$203
Round trip
2026-09-09 – 2026-09-15
CHS - Chicago
67% AI deal score
$253
$204
Round trip
2026-09-29 – 2026-10-26
CHS - Chicago
45% AI deal score
$209
$207
Round trip
2026-09-09 – 2026-10-05
CHS - Chicago
45% AI deal score
$210
$207
Round trip
2026-09-29 – 2026-10-05
CHS - Chicago
66% AI deal score
$249
$207
Round trip
2026-10-03 – 2026-10-10
CHS - Chicago
45% AI deal score
$141
$209
Round trip
2026-10-03 – 2026-10-17
CHS - Chicago
44% AI deal score
$123
$209
Round trip
